The Best Chicago Old Town Bars to Try This Weekend

February 2, 2018 | By Luxury Living Chicago Team
Reading Time: 3 Minutes

These Are The Best Chicago Old Town Bars to Try This Weekend

With over 10 years of experience helping our clients find the perfect apartment or home in Chicago, we can confidently say it is one of the best cities to live in the country.

With a wide assortment of bars that cater to everyone’s taste, Old Town is one of Chicago’s best areas for nightlife. We’ve put together a list of the best bars in Old Town to try out this weekend.


The Vig

The Vig is a 1950’s themed sports parlor that is extra lively on the weekends. With fun cocktails such as Go Fig or Go Home and the classic Vig Old Fashioned, the fun vibe of this weekend hotspot is channeled in the drink menu. Beer lovers will also be happy here as the brew list is extensive. One of the best parts of this bar is the late night menu that starts at 10 PM! Favorites include The Chicken Wings and Mozzarella Stuffed Meatballs. Don’t forget to try the delicious Frosé in the summertime!



Benchmark is a vibrant sports bar that offers a wide assortment of drinks and bar bites. The drink menu features classic cocktails such as a Blackberry Smash and an Old Fashioned. Fun group choices include the shareable cocktails such as the Arnold Palmer which includes Deep Eddy Sweet Tea, Deep Eddy Lemon, blackberries, mint, and sparkling water. They also offer a few great beers on tap and a have a nice wine selection. This bar is the most fun during the warmer weather when the outdoor rooftop patio opens up and allows drinkers to enjoy the summer air.


Old Town Pour House

Old Town Pour House is the place to be in Old Town for the beer lover. With over 90 American craft beers on tap, you’re more than likely to find a new favorite draft beer. With dark wood interior decoration, the classic vibe of this bar along with the wonderful beer selection makes it a great place to watch sports and socialize with friends on the weekend.


The Rabbit Hole

The Rabbit Hole is a rustic-chic bar on North Wells Street that serves upgraded bar food with a great selection of cocktails and drinks. Some creative and fun cocktails include the Pig & Pepper which is watermelon infused Beefeater Gin, mint, basil, Thai chilis, lime juice, combined with a Togarashi pepper spice rim, and a pork belly and herb skewer. For those feeling less adventurous with their cocktails, The Rabbit Hole offers a wide assortment of beers and some ciders.


Marge’s Still

For those with a taste for history, check out Marge’s Still, Chicago’s oldest consecutively running tavern. Serving Chicagoans since 1885, this tavern didn’t let prohibition slow it down. Instead, Marge’s Still operated as an underground speakeasy in the 1920’s, serving bathtub gin prepared on the second floor. Today, this bar is the perfect place to grab a drink on a weekend. The cocktail list is inspired by old-time classics such as a Champagne Cocktail, Old Fashioned, and Sidecar. They also have a nice beer selection and offer specials on Bloody Marys and mimosas during the weekends.


The J. Parker

The J. Parker sits just outside of the Old Town Triangle on the Hotel Lincoln rooftop. With breathtaking views of Lincoln Park and Lake Michigan, this rooftop bar is one to not be missed in the warmer months. The J. Parker offers small bites in addition to a great drink menu with many signature cocktails. The signature cocktails all have a Chicago theme and include the Divine Days, Devil in the White City, House on Mango Street, and Boss. This bar also offers a few carefully selected craft beers and wine by the bottle or glass.


Now that you have a taste of Old Town’s vibrant night scene, it’s time to check out this neighborhood for yourself. If you’re in the market for a new Chicago apartment or condo and want to experience the best spots in Old Town, click the link below!


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